Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13]Br)=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20].[OH2:21]>CS(C)=O.[Cu-]=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:21])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)=[CH:4][C:3]=1[C:19]#[N:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-bromomethylpyrazole (0.6 g, 1.72 mmol) in DMSO (10 mL) was added copper (I) oxide (0.52 g, 3.62 mmol) and water (3 mL). The reaction was stirred at 60° C. overnight. The next day the reaction mixture was filtered through celite. The filtrate was partitioned between ethyl acetate and water. The organic was washed three times with water, brine, dried over sodium sulfate, filtered and concentrated to leave 1-(4-fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole (0.45 g, 92% yield) as pure compound: MS (CI): 286 (M+H)+(100%).
Workup
- filtrationThe next day the reaction mixture was filtered through celite
- customThe filtrate was partitioned between ethyl acetate and water
- washThe organic was washed three times with water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bc9b8a1ee26d4f78812d6db9ec99f9d1
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06339099B1
Reaction notes
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